STEREOCHEMISTRY OF SUBSTITUTED 1-ALKOXYBICYCLO[2.2.2]OCTENES - DIELS-ALDER SYNTHESIS VERSUS TANDEM-MICHAEL STRATEGY

被引：13

作者：

BATESON, JH

SMITH, CF

WILKINSON, JB

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 03期

关键词：

D O I：

10.1039/p19910000651

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reactions of 1-methoxy- and 1 -ethoxy-cyclohexa-1,3-?? dienes with ethyl cinnamate or ethyl 4,4,4-trifluorocrotonate favour the (1RS,2RS,3SR,4RS) (exo-carboxylate) bicyclo[2.2.2]octene stereochemistry, 5,6,9, whereas the bicyclo-octenes derived from 3-alkoxycyclohex-2-enones by Tandem-Michael additions are obtained exclusively as the (1RS,2SR,3RS,4RS) (endo-carboxylate) isomers 16.

引用

页码：651 / 653

页数：3

共 14 条

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